Boron tribromide → HCID 59222981, compound

Participants

Reaction Steps

To a solution of (5,8-difluoroquinazolin-4-yl)-{2-[3-methoxy-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine (2.71 g, 5.69 mmol) in CH2Cl2 (25 mL) cooled to −50° C., was added 1 M BBr3 in CH2Cl2 (17 mL, 17 mmol). The solution was allowed to warm to room temperature and stirred overnight, and then quenched slowly with methanol. The solvent was removed by rotary evaporation and the residue was suspended in chloroform. The product was collected by suction filtration to give 2.70 g (quantitative) of 5-[2-(5,8-difluoroquinazolin-4-ylamino)-ethyl]-2-(4-trifluoromethylpyridin-2-yloxy)-phenol. The product was used in the following reaction without further purification. 1H NMR (CD3OD): δ 8.78 (s, 1H), 8.39 (d, J=5.4 Hz, 1H), 7.93 (m, 1H), 7.54 (m, 1H), 7.45 (d, J=5.4 Hz, 1H), 7.19 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H) 6.87 (dd, J=7.8, 2.1 Hz, 1H), 4.12 (t, J=7.5 Hz, 2H), 3.05 (t, J=7.5 Hz, 2H). LC/MS: 460.97 (M+−1).

Provenance & Evidence